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A4403

Sigma-Aldrich

L-Ascorbic acid

powder, suitable for cell culture, γ-irradiated

Synonym(s):

L-Threoascorbic acid, Antiscorbutic factor, Vitamin C

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About This Item

Empirical Formula (Hill Notation):
C6H8O6
CAS Number:
50-81-7
Molecular Weight:
176.12
Beilstein/REAXYS Number:
84272
EC Number:
200-066-2
MDL number:
MFCD00064328
UNSPSC Code:
12352207
PubChem Substance ID:
24890857
NACRES:
NA.75

biological source

synthetic (organic)

Quality Level

200

sterility

γ-irradiated

form

powder

mol wt

Mw 176.12 g/mol

technique(s)

cell culture | insect: suitable
cell culture | mammalian: suitable
cell culture | plant: suitable

color

white to off-white

pH

1.0-2.5 (25 °C, 176 g/L in water)

mp

190-194 °C (dec.)

solubility

H2O: 10 mg/mL

SMILES string

OC([C@]([C@@H](O)CO)([H])O1)=C(O)C1=O

InChI

1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1

InChI key

CIWBSHSKHKDKBQ-JLAZNSOCSA-N

Gene Information

human ... SLC23A2(9962)

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General description

L-ascorbic acid is an unsaturated γ-lactone ring containing an enediol configuration (–COH=COH) attached with a carbonyl group.

Application

For use in cell culture applications as an antioxidant and to regenerate tocopherol.
L-ascorbic acid has been used:
  • in an osteogenic supplement for the growth of cells
  • as a component in the differentiation media
  • in WS-MSCs (Werner syndrome-mesenchymal stem cells) to study rescuing properties of ascorbic acid on aging defects

Biochem/physiol Actions

L-ascorbic acid mainly exhibits antioxidant properties. It protects plants from oxidative stress and mammals from diseases associated with oxidative stress. L-ascorbic acid mainly protects from hydroxyl radicals, superoxide and singlet oxygen. In addition, it also reduces the membrane-linked antioxidant α-tocopherol (oxidised form). L-Ascorbic acid enhances endothelium-dependent vasodilation in various disorders, including diabetes, coronary artery disease, hypertension and chronic heart failure.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

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Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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Certificates of Analysis (COA)

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Plant L-ascorbic acid: chemistry, function, metabolism, bioavailability and effects of processing.
Davey MW
Journal of the Science of Food and Agriculture, 80, 825-860 (2000)
P L Conklin et al.
Plant physiology, 115(3), 1277-1285 (1997-12-09)
The biosynthesis of L-ascorbic acid (vitamin C) is not well understood in plants. The ozone-sensitive Arabidopsis thaliana mutant vitamin c-1 (vtc1; formerly known as soz1) is deficient in ascorbic acid, accumulating approximately 30% of wild-type levels. This deficiency could result
Xi Wang et al.
Archives of oral biology, 57(9), 1231-1240 (2012-03-30)
This study focused on the characterization of stem cells from human exfoliated deciduous teeth (SHED) in comparison with dental pulp stem cells (DPSCs) to certify SHED as a key element in tissue engineering. In the present study, SHED and DPSCs
R Heller et al.
The Journal of biological chemistry, 274(12), 8254-8260 (1999-03-13)
Ascorbic acid has been shown to enhance impaired endothelium-dependent vasodilation in patients with atherosclerosis by a mechanism that is thought to involve protection of nitric oxide (NO) from inactivation by free oxygen radicals. The present study in human endothelial cells
Ying Li et al.
Protein & cell, 7(7), 478-488 (2016-06-09)
Werner syndrome (WS) is a premature aging disorder that mainly affects tissues derived from mesoderm. We have recently developed a novel human WS model using WRN-deficient human mesenchymal stem cells (MSCs). This model recapitulates many phenotypic features of WS. Based
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